What was the biggest waste of money you ever experienced?

I was just thinking about the $100 million dollars a day that Canada was losing because it doesn't have the pipeline capacity to ship to other sellers and couldn't get a basic building permit passed to build one then I got to thinking about my own personal biggest financial losses or waste of money situations. I have never had too much money so I guess that insulated me from any huge financial loss or mistake. Probably the biggest waste of money was a two year old truck I bought. It was the newest vehicle I ever purchased and thus far - the last. It ended up being a pretty big waste of money because the frame quickly rusted and the transmission lost 5th gear. Wasted money but at least I got some use out of it. Having to sell an almost new dirt bike for close to half of it's worth to pay some bills was another waste of money. At least someone else benefited from the dirt bike... I guess both situations have taught me something. Most of the waste of money that I have experienced are from small things I've purchased so I've been quite fortunate.

What's the biggest waste of money you've experienced and dare to share? Did you throw good money after bad? In retrospect have you figured out a way to tell yourself that it was not all bad and you gained something from the experience? Is there something you've learned from the experience that we can all learn from??

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